Diisopropylethylamine → HCID 67332211, compound

HRID 1896747Notes

Reaction equation

HRID 1896747 reaction equation
[F:1][C:2]([F:9])([F:8])[CH2:3][CH2:4][C:5](O)=[O:6].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.[C:43]1([CH3:59])[CH:48]=[CH:47][C:46]([C:49]2[O:50][C:51]3[CH:57]=[CH:56][C:55]([NH2:58])=[CH:54][C:52]=3[N:53]=2)=[CH:45][CH:44]=1>CN(C)C=O.C(OCC)(=O)C>[F:1][C:2]([F:9])([F:8])[CH2:3][CH2:4][C:5]([NH:58][C:55]1[CH:56]=[CH:57][C:51]2[O:50][C:49]([C:46]3[CH:47]=[CH:48][C:43]([CH3:59])=[CH:44][CH:45]=3)=[N:53][C:52]=2[CH:54]=1)=[O:6]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 7218792-(4-methylphenyl)-1,3-benzoxazol-5-amineHCID 27770854,4,4-Trifluorobutanoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 67332211HCID 67332211, compoundYield 8.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 4,4,4-trifluorobutanoic acid (128 mg, 0.90 mmol) in dry dimethylformamide (5 mL) was added HATU (397 mg, 1.05 mmol) and diisopropylethylamine (496 μL, 2.85 mmol). The mixture was then stirred at room temperature for 10 min. 2-p-Tolylbenzo[d]oxazol-5-amine (200 mg, 0.95 mmol) was then added and the resulting mixture was stirred at room temperature for 16 h. Ethyl acetate was added and the organic layer was washed once with saturated aqueous Na2CO3, followed by another wash with brine. The combined organic layers were dried over anhydrous MgSO4 and evaporated. The resulting solid was purified by column chromatography eluting with ethyl acetate/hexanes 40:60 v/v to afford 26.7 mg (8%) of the title compound (LCMS RT=6.77 min, MH+ 348.9)

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 16 h
  2. washthe organic layer was washed once with saturated aqueous Na2CO3
  3. washanother wash with brine
  4. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  5. customevaporated
  6. customThe resulting solid was purified by column chromatography
  7. washeluting with ethyl acetate/hexanes 40:60 v/v

Sources & evidence

ORD record
ord-61048e0d7e484af19e14a0cb837352fc
Source dataset
uspto-grants-2013_08
Patent number
US08518980B2

Reaction notes

Loading…